diff --git a/packages/toolbox-core/src/toolbox_core/client.py b/packages/toolbox-core/src/toolbox_core/client.py
index 110a1263d..257dd3521 100644
--- a/packages/toolbox-core/src/toolbox_core/client.py
+++ b/packages/toolbox-core/src/toolbox_core/client.py
@@ -30,7 +30,7 @@
 from .protocol import Protocol, ToolSchema
 from .tool import ToolboxTool
 from .toolbox_transport import ToolboxTransport
-from .utils import identify_auth_requirements, resolve_value
+from .utils import identify_auth_requirements, resolve_value, warn_if_http_and_headers
 
 
 class ToolboxClient:
@@ -101,6 +101,7 @@ def __init__(
                 raise ValueError(f"Unsupported MCP protocol version: {protocol}")
 
         self.__client_headers = client_headers if client_headers is not None else {}
+        warn_if_http_and_headers(url, self.__client_headers)
 
     def __parse_tool(
         self,
@@ -224,6 +225,8 @@ async def load_tool(
             for name, val in self.__client_headers.items()
         }
 
+        warn_if_http_and_headers(self.__transport.base_url, auth_token_getters)
+
         manifest = await self.__transport.tool_get(name, resolved_headers)
 
         # parse the provided definition to a tool
@@ -299,6 +302,8 @@ async def load_toolset(
             for header_name in original_headers
         }
 
+        warn_if_http_and_headers(self.__transport.base_url, auth_token_getters)
+
         manifest = await self.__transport.tools_list(name, resolved_headers)
 
         tools: list[ToolboxTool] = []
diff --git a/packages/toolbox-core/src/toolbox_core/tool.py b/packages/toolbox-core/src/toolbox_core/tool.py
index 0c72c39b3..ecc3f568a 100644
--- a/packages/toolbox-core/src/toolbox_core/tool.py
+++ b/packages/toolbox-core/src/toolbox_core/tool.py
@@ -18,7 +18,6 @@
 from inspect import Signature
 from types import MappingProxyType
 from typing import Any, Awaitable, Callable, Mapping, Optional, Sequence, Union
-from warnings import warn
 
 from .itransport import ITransport
 from .protocol import ParameterSchema
@@ -27,6 +26,7 @@
     identify_auth_requirements,
     params_to_pydantic_model,
     resolve_value,
+    warn_if_http_and_headers,
 )
 
 
@@ -272,6 +272,8 @@ async def __call__(self, *args: Any, **kwargs: Any) -> str:
                 token_getter
             )
 
+        warn_if_http_and_headers(self.__transport.base_url, headers)
+
         return await self.__transport.tool_invoke(
             self.__name__,
             payload,
diff --git a/packages/toolbox-core/src/toolbox_core/toolbox_transport.py b/packages/toolbox-core/src/toolbox_core/toolbox_transport.py
index 0f1e7e40d..3f83d8306 100644
--- a/packages/toolbox-core/src/toolbox_core/toolbox_transport.py
+++ b/packages/toolbox-core/src/toolbox_core/toolbox_transport.py
@@ -13,12 +13,12 @@
 # limitations under the License.
 
 from typing import Mapping, Optional
-from warnings import warn
 
 from aiohttp import ClientSession
 
 from .itransport import ITransport
 from .protocol import ManifestSchema
+from .utils import warn_if_http_and_headers
 
 
 class ToolboxTransport(ITransport):
@@ -70,14 +70,6 @@ async def tools_list(
     async def tool_invoke(
         self, tool_name: str, arguments: dict, headers: Mapping[str, str]
     ) -> str:
-        # ID tokens contain sensitive user information (claims). Transmitting
-        # these over HTTP exposes the data to interception and unauthorized
-        # access. Always use HTTPS to ensure secure communication and protect
-        # user privacy.
-        if self.base_url.startswith("http://") and headers:
-            warn(
-                "Sending data token over HTTP. User data may be exposed. Use HTTPS for secure communication."
-            )
         url = f"{self.__base_url}/api/tool/{tool_name}/invoke"
         async with self.__session.post(
             url,
diff --git a/packages/toolbox-core/src/toolbox_core/utils.py b/packages/toolbox-core/src/toolbox_core/utils.py
index 08a87a451..1f34c4bef 100644
--- a/packages/toolbox-core/src/toolbox_core/utils.py
+++ b/packages/toolbox-core/src/toolbox_core/utils.py
@@ -14,6 +14,7 @@
 
 
 import asyncio
+import warnings
 from typing import (
     Any,
     Awaitable,
@@ -43,6 +44,14 @@ def create_func_docstring(description: str, params: Sequence[ParameterSchema]) -
     return docstring
 
 
+def warn_if_http_and_headers(url: str, headers: Mapping[str, Any] | None) -> None:
+    """Logs a warning if the url uses HTTP and sensitive headers are present."""
+    if url.lower().startswith("http://") and headers:
+        warnings.warn(
+            "This connection is using HTTP. To prevent credential exposure, please ensure all communication is sent over HTTPS."
+        )
+
+
 def identify_auth_requirements(
     req_authn_params: Mapping[str, list[str]],
     req_authz_tokens: Sequence[str],
diff --git a/packages/toolbox-core/tests/test_tool.py b/packages/toolbox-core/tests/test_tool.py
index 822cc6b9e..0f0286af8 100644
--- a/packages/toolbox-core/tests/test_tool.py
+++ b/packages/toolbox-core/tests/test_tool.py
@@ -685,3 +685,68 @@ async def test_bind_param_chaining(
             json={"count": 42, "message": "chained-call"},
             headers={},
         )
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "base_url, headers, should_warn",
+    [
+        (
+            "http://fake-toolbox-server.com",
+            {"Authorization": "Bearer token"},
+            True,
+        ),
+        (
+            "https://fake-toolbox-server.com",
+            {"Authorization": "Bearer token"},
+            False,
+        ),
+        ("http://fake-toolbox-server.com", {}, False),
+        ("http://fake-toolbox-server.com", None, False),
+    ],
+)
+async def test_tool_call_http_warning(
+    http_session: ClientSession,
+    base_url: str,
+    headers: Mapping[str, str] | None,
+    should_warn: bool,
+):
+    """Tests the HTTP security warning logic during tool invocation via __call__."""
+    url = f"{base_url}/api/tool/{TEST_TOOL_NAME}/invoke"
+    args = {"param1": "value1"}
+    response_payload = {"result": "success"}
+    transport = ToolboxTransport(base_url, http_session)
+
+    tool = ToolboxTool(
+        transport=transport,
+        name=TEST_TOOL_NAME,
+        description="A tool",
+        params=[
+            ParameterSchema(name="param1", type="string", description="param1 desc")
+        ],
+        required_authn_params={},
+        required_authz_tokens=[],
+        auth_service_token_getters={},
+        bound_params={},
+        client_headers=headers if headers is not None else {},
+    )
+
+    with aioresponses() as m:
+        m.post(url, status=200, payload=response_payload)
+
+        if should_warn:
+            with pytest.warns(
+                UserWarning,
+                match="This connection is using HTTP. To prevent credential exposure, please ensure all communication is sent over HTTPS.",
+            ):
+                await tool(param1="value1")
+        else:
+            # Check no warnings fired
+            with catch_warnings(record=True) as record:
+                simplefilter("always")
+                await tool(param1="value1")
+
+            warning_messages = [str(w.message) for w in record]
+            assert not any(
+                "This connection is using HTTP" in msg for msg in warning_messages
+            )
diff --git a/packages/toolbox-core/tests/test_toolbox_transport.py b/packages/toolbox-core/tests/test_toolbox_transport.py
index 2921e09f8..84944274f 100644
--- a/packages/toolbox-core/tests/test_toolbox_transport.py
+++ b/packages/toolbox-core/tests/test_toolbox_transport.py
@@ -154,48 +154,6 @@ async def test_tool_invoke_failure(http_session: ClientSession):
     assert str(exc_info.value) == "Invalid arguments"
 
 
-@pytest.mark.asyncio
-@pytest.mark.parametrize(
-    "base_url, headers, should_warn",
-    [
-        (
-            "http://fake-toolbox-server.com",
-            {"Authorization": "Bearer token"},
-            True,
-        ),
-        (
-            "https://fake-toolbox-server.com",
-            {"Authorization": "Bearer token"},
-            False,
-        ),
-        ("http://fake-toolbox-server.com", {}, False),
-        ("http://fake-toolbox-server.com", None, False),
-    ],
-)
-async def test_tool_invoke_http_warning(
-    http_session: ClientSession,
-    base_url: str,
-    headers: Optional[Mapping[str, str]],
-    should_warn: bool,
-):
-    """Tests the HTTP security warning logic in tool_invoke."""
-    url = f"{base_url}/api/tool/{TEST_TOOL_NAME}/invoke"
-    args = {"param1": "value1"}
-    response_payload = {"result": "success"}
-    transport = ToolboxTransport(base_url, http_session)
-
-    with aioresponses() as m:
-        m.post(url, status=200, payload=response_payload)
-
-        if should_warn:
-            with pytest.warns(UserWarning, match="Sending data token over HTTP"):
-                await transport.tool_invoke(TEST_TOOL_NAME, args, headers)
-        else:
-            # By not using pytest.warns, we assert that no warnings are raised.
-            # The test will fail if an unexpected UserWarning occurs.
-            await transport.tool_invoke(TEST_TOOL_NAME, args, headers)
-
-
 @pytest.mark.asyncio
 async def test_close_does_not_close_unmanaged_session():
     """
diff --git a/packages/toolbox-core/tests/test_utils.py b/packages/toolbox-core/tests/test_utils.py
index b3ddd7c33..1f54ae0dc 100644
--- a/packages/toolbox-core/tests/test_utils.py
+++ b/packages/toolbox-core/tests/test_utils.py
@@ -14,6 +14,7 @@
 
 
 import asyncio
+import warnings
 from typing import Type
 from unittest.mock import Mock
 
@@ -26,6 +27,7 @@
     identify_auth_requirements,
     params_to_pydantic_model,
     resolve_value,
+    warn_if_http_and_headers,
 )
 
 
@@ -458,3 +460,31 @@ async def another_async_func():
         return {"key": "value"}
 
     assert await resolve_value(another_async_func) == {"key": "value"}
+
+
+def test_warn_if_http_and_headers_triggers():
+    """Test that a warning is emitted for HTTP URLs with headers."""
+    url = "http://example.com"
+    headers = {"Authorization": "Bearer token"}
+    with pytest.warns(UserWarning, match="This connection is using HTTP"):
+        warn_if_http_and_headers(url, headers)
+
+
+def test_warn_if_http_and_headers_no_headers():
+    """Test that no warning is emitted for HTTP URLs without headers."""
+    url = "http://example.com"
+    headers = {}
+    with warnings.catch_warnings(record=True) as w:
+        warnings.simplefilter("always")
+        warn_if_http_and_headers(url, headers)
+        assert len(w) == 0
+
+
+def test_warn_if_http_and_headers_https():
+    """Test that no warning is emitted for HTTPS URLs."""
+    url = "https://example.com"
+    headers = {"Authorization": "Bearer token"}
+    with warnings.catch_warnings(record=True) as w:
+        warnings.simplefilter("always")
+        warn_if_http_and_headers(url, headers)
+        assert len(w) == 0